From support today
“Hi Chris,
This is not something that we at MSFS Support can fix for you currently. We shared your previous messages as feedback.
The new imagery has been delayed and will be released once it is ready.
I do not know if the Chicago area will get added photogrammetry. This has never been promised. There was supposed to be new imagery added in MSFS / MSFS 2024 by the end of this year, but that has been delayed due to the MSFS 2024 release.
Adding new imagery is not a simple process. All this must go through thorough testing. When it is ready for release, it will be released.”